Interested in exploring Chicago from the perspective of ghosts and gangsters? Want to really immerse yourself in the history of this great American city, right from the locations that started it all? This tour visits the locations frequented by some of Chicago’s most notorious gangsters along with many of the most haunted locations in Chicago! You can get the best of both worlds with this 2 in 1, history-based guided walking tour of Chicago’s gangsters and ghost stories, right from the famous Chicago Loop Vice District! Upgrade to the bus tour option to experience the same spine-chilling stories by minibus. Includes one stop for an immersive experience.

Escape into Chicago’s underworld on a crime and mob tour with stops on-and-off the luxury, climate-controlled bus. Explore historic crime scenes with great photo opportunities. Hear true crime stories about Chicago Gangster Al Capone, The Untouchables, The Chicago Mob, Prohibition, John Dillinger, Frank “The Enforcer” Nitti, Cap George Streeter, Leopold & Loeb, H.H. Holmes and more. Visit historic landmark buildings like: The Biograph Theater, Holy Name Cathedral, Cook County Criminal Court House, Harry Caray’s Italian Steakhouse, etc. Tour famous Chicago neighborhoods: Streeterville, River North, Gold Coast, Lincoln Park, Old Town, Loop and Magnificent Mile. Locals and tourists agree that this educational and entertaining thing to do in Chicago is a unique cultural experience.

Taste some of Chicago’s most iconic foods while walking through one of the Prohibition Era’s most fashionable and notorious neighborhoods. Sample prime steak, deep dish pizza and the world famous “Chicago hot dog” while treading the streets of Capone’s closest friends and dreaded enemies. Even visit an old tunnel used by prohibition gangsters in the basement of one of the establishments! Learn about Chicago’s world famous cuisine and the gangsters who ate it all in one special unique tour!

Discover Chicago’s captivating past on our top-rated Gangsters and Ghosts luxury minibus tour, exploring the iconic Loop and River North neighborhoods, once dominated by notorious Italian and Irish gangs during Prohibition. Delve into the city’s infamous organized crime history and hear spine-chilling tales from our expert guide about the ghosts that still roam these streets. The tour features 1 stop for an immersive experience, allowing you to witness Chicago’s history firsthand. Interested in exploring Chicago from the perspective of ghosts and gangsters? Want to really immerse yourself in the history of this great American city, right from the locations that started it all? This tour visits the locations frequented by some of Chicago’s most notorious gangsters along with many of the most haunted locations in Chicago!

Join this Chicago haunted pub tour which is a combination ghost tour and pub crawl that will take you on a walking tour to explore the fascinating history of Chicago and hear some of its most famous and creepy haunted stories. A costumed guide will lead tour goers on a 2.5-hour journey, offering glimpses into the past and revealing the stories of long-dead phantoms and specters who still call Chicago home. You’ll visit several different bars and have time to enjoy a delicious libation (at own expense) as the guide tells them about all the spooky happenings and great history of this town! *Tour route and drink stops are subject to availability. *All guests must be 21+ with Valid ID. Alcohol is not included.

Our guides present an accurate account of the activities in Chicago during the 1920’s and 1930’s (Prohibition Era). You will hear about the exploits of Capone, Moran, Dillinger and the rest of the boys! Some sites included are: the St. Valentine’s Day Massacre, the Biograph Theater, and Holy Name Cathedral. The tour is educational but also very entertaining because our Gangster Guides are actors. Our Untouchable Tour Gangster Guides take on the persona of a gangster and have fun with it. Reservations are strongly recommended.

Often imitated but never matched, this 3 hour ghost bus tour with stops remains the “Best of Chicago” since its founding 23 years ago by the city’s ghostlorist, Ursula Bielski. Ursula and her team of veteran paranormal researchers and historians have thrilled thousands of guests with firsthand experiences of this, one of the world’s most legendarily notorious cities. We take you where the other walking tours simply can’t–to the many shadowed corners where the fateful tales began. From the Fort Dearborn Massacre to the St. Valentine’s Day Massacre. From the Great Chicago Fire to the Eastland Disaster. From ghost ships that sail Lake Michigan to the Chicago origins of “Ghostbusters” And to the lair of the Devil Baby of Hull House.

Come on our chilling ghost tour presented by US Ghost Adventures! Book Directly With Windy City Ghosts and save $5/person. Windy City Ghosts walking Ghost Tour provides a look into the darkness that lurks below Chicago’s busy streets. Our Ghost Tour transports you back in time to an era of gangsters, bootleggers, bank robbers, and jazz babies. Windy City Ghosts nightly Ghost Tours take you through Lincoln Park, a beautiful North Side neighborhood with a twisted past. Learn about the forgotten burial ground that is the foundation of this bustling neighborhood. Check the bathroom mirrors in the Lion House of the Lincoln Park Zoo to make sure the ghost of a Victorian woman in white isn’t standing right behind you. Learn what spirit haunted Al Capone to the end of his days. On our Ghost Tour, you’ll hear the strange and disturbing tales associated with each of our carefully selected tour stops.

Join us for a fun night of exploring Chicago’s crime history on this 2-2.5-hour bus tour that includes: * World famous crime scenes like the St Valentine’s Day massacre * Stops on-and-off the bus at famous crime sites * True Crime history * Historic video footage * Interactive live commentary * Crime quiz * Souvenir pamphlet with photos * Luxury climate-controlled bus * So much more! Some of the world’s most notorious criminals, mobsters & gangsters bamboozled their way through Chicago. Escape into the city’s criminal underworld as you investigate stories about Al Capone, The Untouchables, the Chicago Mob and more. From a luxury coach, see the sites of storied crime scenes including Biograph Theatre, Holy Name Cathedral, and the St Valentine’s Day Massacre, one of Chicago’s most notorious murders. Snap photos of the historic criminal courthouse, and hop on-and-off the coach to walk the path that Chicago gangsters John Dillinger and Hymie Weiss followed just before their deaths.

Looking for thrilling things to do in Chicago at night? Join Absolutely Chicago Segway Tours for a haunted ghost and gangster tour! Glide through downtown Chicago, discovering the city’s chilling history of death, disasters, murders, and ghostly tales. Visit haunted landmarks like Buckingham Fountain, where you’ll hear about Al Capone’s haunted yacht and a notorious Michigan Avenue hotel. Explore Death Alley, site of the Iroquois Theatre fire, and the Chicago River, home to the tragic Eastland Disaster. This spooky Chicago night tour is a fun and eerie way to experience the city’s dark side! We offer this tour more frequently as we get closer to the Halloween season.

We are Chicago’s only paranormal investigation tour, and Chicago’s oldest ghost and hauntings tours, founded by Ursula Bielski, Chicago’s 35 year paranormal researcher and investigator. Like Ursula, all of our guides are all real investigators and true Chicagoans. We love investigating, we love Chicago history, and we would love to show you Chicago’s haunted history. This is the only tour which takes you out of the downtown area and into one of the most haunted parts of Chicago: Lincoln Park, the old City Cemetery, which was ravaged by the Great Fire of 1871, leaving 10,000 graves behind. The bodies are all still here, as well as the ghosts. The tour also visits the site of the St. Valentine’s Day Massacre and the site of Suicide Bridge, where more than 100 desperate souls lost their lives.

CHOOSE from our range of discounted tour passes below & save up to $55 per person! Children aged 0-6 are free! Hassle free booking – no referral to third party operators, we own all of the tours! 5 tour pass – SAVE $55 PER PERSON (redeemable March – Oct) -Gangster & Food Walking Tour -Secret Interior Architectural Walking Tour -Gangsters & Ghosts Minibus Tour -Luxury Minibus City Sightseeing Tour -Riverboat Architecture Tour 4 tour pass – SAVE $40 PP (redeemable year-round) -Gangsters Food Walking Tour -Secret Interior Architectural Walking Tour -Gangsters & Ghosts Minibus Tour -Luxury Minibus City Sightseeing Tour 3 tour pass – SAVE $25 PP (redeemable March – Oct) -Riverboat Architecture Tour -Secret Interior Architectural Walking Tour -Gangsters & Ghosts Walking Tour 2 tour pass – 2 TOURS FOR THE PRICE OF 1 (redeemable year-round) -Secret Interior Architectural Walking Tour -Gangsters & Ghosts Walking Tour All tours are led by an expert tour guide. Book now for the best value!

The Windy City is known for its food, architecture, and haunting history! Walk with us as the sun sets through downtown Chicago, hearing some of the most gruesome and creepy Chicago stories. The first stop is the Congress Hotel, the most haunted hotel in Chicago. Walk along the streets that H. H. Holmes, Chicago’s first serial killer, wandered as he stalked his prey, get a glimpse of Chicago’s sordid past through stories of the Everleigh Club and the 1900s Red Light district, and learn about downtown prison breaks.

Up for more of a spooky perspective of the Windy City? Boy, does it deliver. We have curated a unique and underground ghost tour, providing you with the rare opportunity to visit many of Chicago’s notable haunted locations.  • Murder Castle: the hotel designed specifically for murdering people in the late 1800s by America’s first mass serial killer: H.H. Holmes. • Death Alley: Peruse a haunting pathway where hundreds of theater patrons were stacked after perishing in the great fire at the Iroquois Theater • Old Congress Hotel: Once the full time residence of its former owner, Al Capone, there are ghosts and spirits that haunt the hallways of this famed location. Different from other tours, our Haunted Chicago Tour is guided by a historian, providing insight into the historical events, information, persons, and rumors of the past. 

Fell the tug of history and dive into the breathtaking events of the past. On this intriguing and unusual tour, you will explore another side of famous locations and get acquainted with haunted places filled with a spirit of gangsters and speakeasies of the roaring 20s. Hear the captivating stories of Chicago’s past and feel the curiosity level rising as you immerse yourself into those times. Discover the dark and mysterious history of the Chicago downtown Be entertained by the expert local guide who knows the true history of the city Get to know what lies beyond the famous Chicago facades and what is hidden from the mainstream tours Visit the most impressive and exciting sites.

Chicago’s original Millionaire’s Row, meet the ghosts of the Gilded Age. Marshall Field, George Pullman, Philip Armour, and many more used to live in this amazing area, the most desirable address in the city before the fire. Many of the incredible homes are still standing and the spirits linger, waiting to divulge their secrets in a haunted history tour and ghost investigation in one of Chicago’s most prestigious places.

Our Prohibition Era Speakeasy Pub Crawl is filled with cocktails and a perfect venue for bachelor or bachelorette parties, corporate events, or just a fun night out on the town to celebrate life and your friends. Hosted by a local historian, the tour makes stops at: • Al Capone’s neighborhood • Old Chicago bars • Prohibition era establishments  We transport you back in time to the 1920s, entering our venues through secret openings that really shed light on what the city was like 100-years ago. Relive the glamour of this time period while listening to stories of the rampant racketeering and bootlegging. If you’re really feeling up to it, dress the part, too.

Embark on a thrilling journey down one of the most haunted roads in the world, Archer Avenue. A mere stone’s throw from Chicago, this historic Indian trail cuts through the industrial heartlands of Bedford Park and Summit, and winds down to the lush, verdant expanses of the Forest Preserve District of Cook County. Haunted by ghost lights and vanishing hitchhikers, Archer Avenue is steeped in stories of sorrow and tragedy. It’s a road marked by the tears of laborers, victims of ghastly crimes, and countless mourners who have carried their loved ones to their final resting places in the seven cemeteries that border it. Constructed by Irish workers on the Illinois and Michigan Canal in the 1830s and ’40s, Archer Avenue has become the epicenter of Chicago’s supernatural forces. Join our ghost tour and uncover the chilling secrets of this haunted highway.

Uncover Hollywood’s sinister past in Chicago through The Wizard of Oz, cocaine movies, and gangsters! A park inspired by The Wizard of Oz, homes designed by Chicago’s leading architect, and a theater built for moving pictures seem friendly enough. But a closer look at these Chicago locations leads us down a destructive path closely tied to Hollywood. Along your journey, film clips, screenshots, newspaper clippings, and vintage movie magazines will transport you back in time, offering glimpses into scandalous happenings of yesteryear. Join Chicago Movie Tours in Chicago’s Lincoln Park neighborhood for this 90-minute guided outdoor walking tour on the darker side of the silver screen, with special focus on the 1939 movie musical The Wizard of Oz. WAIVER Guests must initial a digital general waiver of liability after they book. CHILDREN While this tour does explore the children’s story The Wizard of Oz, some content may not be appropriate for guests under age 13.

Chicago and the history of the mob are synonymous when we look back at history. That’s why we provide an in-depth Chicago Gangster Tour that makes all of the infamous stops for our patrons.  Visit the old stomping grounds of: • Al Capone • John Dillinger • The Untouchables View crime scenes immortalized in vintage news footage, the theater where the law caught up with Dillinger, the restaurant where the North Side Gang riddled Al Capone’s motorcade with rounds from their Tommy Guns, and the site of the St. Valentine’s Day Massacre. We bring Chicago’s true crime past to life before your very eyes.

We wrote the book(s) on Chicago ghosts! Now in our 24th year! Ursula Bielski, our founder, has published more than a dozen volumes on Chicago’s haunted history over more than two decades. Chicago Hauntings is the original Chicago ghost tour and still the best. Our tours are based on all original research, unlike the many other knock-off tours you’ll find today. Beware of the imitations. Imagine walking in the steps of Chicago’s most notorious criminals at the city’s original courthouse, putting your fingers into actual bullet holes from Chicago’s gangland days, feeling the haunting presences near the site of the old Cook County gallows, and gazing upon the waters where 844 souls lost their lives in the horrific Eastland disaster of 1915. Come along and experience all this and more. We are also the only interactive tour experience where YOU are the paranormal investigator, using simple tools to look for spirits while you hear tales of Chicago’s most haunted locations.

Join us for the most memorable experience you will have while visiting Chicago! For runners from around the world, this is definitely a “bucket list” activity. This casual paced, guided running tour will take you through and around the most iconic sights that Chicago has to offer. We will take you along the Lake Michigan shoreline where you will take in the most spectacular views of the beautiful city skyline, through Downtown and “the Loop” to cross the Chicago River where we will share some of the incredible history that has made Chicago so famous, from gangsters to marine disasters, and finally up Michigan Avenue to enjoy the cultural and architectural highlights of the Chicago Art Institute, famous historical building and so much more! You will not break any personal best running times, though, as we make stops along the way to talk about the sights and take pictures for you to share with friends and loved ones!

Let us put the Custom in Chicago Custom Tours. What are your must-see venues? What would personalize your excursion? We’ll plan your tour and make it happen, and also provide suggestions based on your interests.

“Lincoln Park Spirits: A Ghostly Walk Through Chicago’s Past” takes you on an eerie exploration of the Lincoln Park neighborhood. Begin at Julia Porter Park, a serene spot with a hidden history. Then, venture past the Alphawood Foundation, a place surrounded by Chicago’s architectural charm and possibly, its spectral tales. Stop by The Red Lion Pub, known for its ghost stories and historical allure. Visit the Victory Gardens Theater, a cultural landmark with its own ghostly rumors. Conclude at Oz Park, a whimsical space that might hold more than just memories of the famous story. This tour is perfect for those who love to explore the mysterious and paranormal side of Chicago.

Come get spooked on Bobby’s Fright Hike! Bobby’s Bike Hike is America’s longest running city bicycle company, and this is Chicago’s premiere Halloween ghost tour. Hop on two wheels and follow Bobby’s expert tour guides through some of the most paranormal and frightening spots in the Windy City. This 3-hour guided bicycle tour explores the uber-haunted John Hancock Center, the site of the SS Eastland Disaster (one of the deadliest shipwrecks in American history), the 200-year old ghosts of the Congress Plaza Hotel, and more! This is the perfect outdoor activity for anyone looking to explore Chicago after dark. Connect with your inner ghost hunter and sign up today!

Start your immersive walking tour at a Chicago icon: the Centennial Fountain at River Esplanade Park. From here, your guide will take you on a culinary and cultural adventure. Our first stop is the famous Billy Goat Tavern, where we recommend trying their signature “cheezborger.” Next, we’ll visit Pizzeria Uno, birthplace of Chicago’s legendary deep-dish pies. Then it’s on to Mr. Beef, home of the classic Chicago Italian beef sandwich and filming location for “The Bear.” Along the way, you’ll hear about the (usually) friendly rivalry with New York’s pizza scene, Chicago’s meatpacking roots, 1920s speakeasies, gangsters, and much more. We recommend you bring around $30 for optional food purchases throughout the tour. Your guide will have tips on what to try at each stop. Our tour ends at the historic Green Door Tavern, where you can soak up its hip, vintage vibes as you wind down the afternoon.

Join us along the historic streets and alleys of Chicago as we walk among the spirits of mobsters and ghosts of the condemned. This tour is for lovers of history, true crime, and haunted mysteries. Expect a sultry and gritty cocktail of Chicago’s darkest stories hiding in the shadows of the Loop. From Grant Park to the Alley of Death, your expert local guide will shed light on the city’s secrets. Prepare for thrills and just the right amount of chills.

See Chicago through the eyes of Al Capone and the Everleigh Sisters at your own pace with this affordable walking tour. • Walk in the footsteps of the gangsters, bootleggers, hoodlums, gunmen, and crooked cops and politicians who made up what was known as the “Chicago Outfit” • Hear from producer Richard Junger, an urban historian, professor and author passionate about Chicago • Do it all in 45 minutes or linger at stops along the way with complete control over when you start and finish • Get unlimited use before your booking date and after it • Use the virtual tour option at home Once you’ve booked, you’ll receive a ticket with instructions and a unique code listed under “Before You Go”. Then simply install the VoiceMap app and enter your code. The app displays directions to the starting point, and when you’re in the right place, just pop in your headphones and tap start. VoiceMap has automatic GPS playback, with turn-by-turn directions. It also works offline.